Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones

Hyung Seok Yoo; Jeong Won Shin; Yoon Hu Jang; Yo Sep Yang; Seung Hwan Son; Hyuck Jae Won; Soo Lim Kim; Jaehoon Sim; Nam Jung Kim

doi:10.1021/acs.joc.3c02558

Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones

Hyung Seok Yoo, Jeong Won Shin, Yoon Hu Jang, Yo Sep Yang, Seung Hwan Son, Hyuck Jae Won, Soo Lim Kim, Jaehoon Sim, Nam Jung Kim

Research output: Contribution to journal › Article › peer-review

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Abstract

An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels-Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90% yield. Kinetic analysis supporting our proposed mechanism was also performed, underscoring the robustness of the developed synthetic pathway.

Original language	English
Pages (from-to)	3102-3110
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	89
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.3c02558
Publication status	Published - 1 Mar 2024

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© 2024 American Chemical Society

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10.1021/acs.joc.3c02558

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Yoo, H. S., Shin, J. W., Jang, Y. H., Yang, Y. S., Son, S. H., Won, H. J., Kim, S. L., Sim, J., & Kim, N. J. (2024). Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones. Journal of Organic Chemistry, 89(5), 3102-3110. https://doi.org/10.1021/acs.joc.3c02558

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title = "Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones",

abstract = "An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels-Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90% yield. Kinetic analysis supporting our proposed mechanism was also performed, underscoring the robustness of the developed synthetic pathway.",

author = "Yoo, {Hyung Seok} and Shin, {Jeong Won} and Jang, {Yoon Hu} and Yang, {Yo Sep} and Son, {Seung Hwan} and Won, {Hyuck Jae} and Kim, {Soo Lim} and Jaehoon Sim and Kim, {Nam Jung}",

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year = "2024",

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doi = "10.1021/acs.joc.3c02558",

language = "English",

volume = "89",

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Yoo, HS, Shin, JW, Jang, YH, Yang, YS, Son, SH, Won, HJ, Kim, SL, Sim, J & Kim, NJ 2024, 'Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones', Journal of Organic Chemistry, vol. 89, no. 5, pp. 3102-3110. https://doi.org/10.1021/acs.joc.3c02558

Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones. / Yoo, Hyung Seok; Shin, Jeong Won; Jang, Yoon Hu et al.
In: Journal of Organic Chemistry, Vol. 89, No. 5, 01.03.2024, p. 3102-3110.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones

AU - Yoo, Hyung Seok

AU - Shin, Jeong Won

AU - Jang, Yoon Hu

AU - Yang, Yo Sep

AU - Son, Seung Hwan

AU - Won, Hyuck Jae

AU - Kim, Soo Lim

AU - Sim, Jaehoon

AU - Kim, Nam Jung

PY - 2024/3/1

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N2 - An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels-Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90% yield. Kinetic analysis supporting our proposed mechanism was also performed, underscoring the robustness of the developed synthetic pathway.

AB - An approach to 2,3-benzotropone from 1-benzosuberone via palladium(II)-catalyzed aerobic dehydrogenation was developed. This method first provided a catalytic route to various 2,3-benzotropones from their corresponding 1-benzosuberones in good yields. In addition, the reaction could be applied to a one-pot Diels-Alder reaction with maleimide, providing a complex benzobicyclo[3.2.2]nonenone in ≤90% yield. Kinetic analysis supporting our proposed mechanism was also performed, underscoring the robustness of the developed synthetic pathway.

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Synthesis of 2,3-Benzotropones via Palladium(II)-Catalyzed Aerobic Dehydrogenation from 1-Benzosuberones and Sequential Diels-Alder Reaction to Yield Benzobicyclo[3.2.2]nonenones

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